So three things come to mind:
1. My best team ever was in a novelty league ("Hitters Paradise") similar to Chicks DIg the Longball (main differences: 200m cap, 1.0m instead of .85 relievers and any stadium)
Won Championship, 108-54, but most noteworthy is the team had a +619 run differential (regular season)
https://365.strat-o-matic.com/league/4486412. My "Worst" team ever: Few months ago we tried a a novelty league where every one tried to lose. Managed to go 50 -112 then lost my semifinal round (by winning 4 games) to the one team that absolutely had my number.
https://365.strat-o-matic.com/league/4579323 My own special 100+ win game curse (which I guess is kind of my favorite/most hated SOM story)
I have not had a ton of 100+ win teams, 6 to be exact (not counting the 112 loss team above that is too weird to figure in). I have extraordinary good luck with those teams, winning 5 out of 6 championships. But it is the team that did not win a championship that haunts me:
The scene, 2019 Barnstormers. We have just finished the regular season of the Sixth event and on the strength of my 100 wins I am sitting on the bubble of making the top 9 for the finals. I am facing a team with a losing record in the Semi's (who admittedly I had only gone 6-6 with during the regular season). I feel pretty good about my chances. I am calculating who needs to win what to get past me. In the end I did not need to win the championship to make the Barnstormer Finals, I did not need to even make the league finals to make the Barnstormer finals. In the end, I needed to win 2 games in the Semi's to make the Barnstormer Finals.
I got swept.
https://365.strat-o-matic.com/league/441228